Emulsifier and method of making same



United States Patent 3,158,487 EMULSHIER AND METHOD OF MAKING SAME Edward J. Reid, Dumont, N..l., assignor to Lever Brothers Company, New York, N.Y., a corporation of Maine No Drawing. Filed Mar. 28, 1961, Ser. No. 98,775 8 Claims. (Cl. 99-94) This invention relates to lactic acid emulsifiers and more particularly to lactylated mixed esters suitable for use as shortening ingredients.

In recent years, it has been proposed to prepare emulsifiers by reacting lactic acid with In accordance with the present invention, it has been found that improved emulsifiers can be prepared by reacting lactic acid with a mixture of the higher fatty acid esters of glycerol and the higher fatty acid esters of pro pylene glycol.

One advantage to the present invention is in the use of ctylated method than that utilized to prepare other commercially available lactylated emulsifiers.

Percent Glyceryl monoester 22.4 Glyceryl diester 21.8 Glyceryl triester 5.8 Propylene glycol monoester 33.4 Propylene glycol diester 16.6

. The mixed partial esters are then heated to l60'l65 and lactic acid is slowly added to esterify (lactylate) at least some of the free hydroxyl groups in the mixed esters. The water evolved is removed from the reaction by a stream of inert gas, and the lactylated product is I'lltered and washed with hot Water. net is improved if a small amount minimizes acid polymers during the reaction.

In the event complete lactylation is desired, it would be advantageous to esterify all hydroxyl groups. complete lactylation is not necessary to produce eflective emulsifiers. A product which is about 80% lactylated, for example, still has the ability to perform in a satisfactory manner as an emulsifying agent.

A The mixed fatty acid esters of glycerol and propylene glycol contain free hydroxyl radicals as the only groups available for reaction with lactic acid and esterification occurs between the hydroxyl radicals of the esters andthe carboxyl group of the lactic acid. Since the hydroxyl Polyhydric alcohol to fatty a'iiIIIIIIII The triglycerides used in the ester interchange with propylene glycol and glycerol may be derived from any animal or vegetable This includes unsaturated fatty nut oil, cottonseed oil, etc.

While it is desirable that at least 10% of the lactylated esters be lactylated propylene glycol monoester, it appears doubtful that this percentage would exceed when trigylcerides are used as the fatty acid source. The proalcohol in the mixture can be widely The ratios tive, however, are

By M01 Wt. By Weight Glycerol to propylene glycol 0.7 to 1.0 0.847 to 1.0. 1.133 to 1.0-"- 0.332 to 1.0.

An increase in the glycerol to propylene glycol ratio would increase the amount of glycerol partial esters while a decrease in this ratio would increase the propylene glycol partial esters. Increasing the ratio of polyhydric alcohol to fatty acid would increase both the glycerol and propylene glycol monoester contents while decreasing both diester contents and the glycerol triester content. The reverse would be true if this ratio were decreased.

Instead of the step of ester interchange with fatty acid triglycerides, free fatty acids or mixtures of fatty acids derived from vegetable or animal oils rect esterification with the alcohols.

portion of liquid ingredients.

In the cake mix type shortening, the lactylated esters derived predominantly from saturated fatty acids are much more effective than the esters prepared from unsaturated acids.

Furthermore, the lactylated esters may be used as the emulsifying agent in the preparation of aerosol whipped toppings or in powdered dessert toppings to replace the 1961, acids should be used to prepare a lactylated mixed ester having the most desirable properties.

In the preparation of shortenings, the lactylated mixed esters of propylene glycol and glycerol may be combined with other well-known emulsifiers including the mono-diglycerides of animal and vegetable oils and fats.

and other'conventional shortening emulsifiers. This substitution of mixed partial esters of propylene glycol and glycerol for mono-diglycerides represents an important advantage since the mixed esters are less expensive to manufacture than the mono-diglycerides.

For best results, the lactylated emulsifier of the present invention is incorporated in shortenings at a level of about 8-16% by weight of the shortening, with the The cakes were prepared as follows: The flour, sugar, non-fat milk solids, baking powder and salt were placed in a Kitchen Aid Mixer bowl. The shortening and twothirds of the water were blended at speed 1 for 30 seconds and the mixture was beaten for 2 minutes at remainder being the conventional animal or vegetable speed 4. The whole eggs were added to the batter and tatsv or oils. Where the lactyl'ated mixed esters are to blended at speed 1 followed by beating at speed 4 be combined with mono-diglycerides or non-lactylated for 1 minute. The remaining water was blended into mixed esters, the shortening contains about 816% by the batter at speed 1" and the batter was beaten for weight of total emulsifier with the ratio of lactylated 1() one minute at specdl. 410 grams of batter were scaled mixed ester to non-lactylated mixed ester or mono-diinto each of two 8 layer pans. The caxes were baked glyceride being about 1:3 to 3:1. at 350 F. for 35 minutes:

In the following examples which further illustrate the The shortening ingredients comprised a blend of 85 compositions of this invention, the lactylated emulsifiers TV. soybean oil and emulsifiers identified as A, B, C, and were prepared as follows. D. Mixtures of lactylated and non-lactylated emulsifiers.

Preparation of the mixed partial esters .l762 grams were also used in the cake baking tests. The results in of soybean oil (1 I.V.), 73.5 grams of glycerol, 312 terms of cake volumes (measured in cubic centimeters) grams of propylene glycol and 1.8 grams of sodium hyare listed in Table I. Unless otherwise noted, the cake droxide were charged to'a reaction vessel equipped with volume was considered a good index of overall cake a mechanical agitator. The mixture was heated to 205 quality.

215' C. with agitation and held at this temperature for The shortenings were prepared by melting the emulsiapproximately one hour. Upon cooling the mixture to tying agent in the soybean oil. on a steam bath, the tem- 160" C., 3.5 grams of 85% ortho phosphoric acid were perature being at least 70 C. The hot liquid was quickadded to the mixture. After stripping the mixture with chilled and textured in a laboratory texturator. This steam at 160 C. for minutes at a pressure of 4 mm. 25 equipment also occludes air in the shortening. The sam- Hg, the mixture was cooled and filtered. ples referred to in Table 1 contained 10% occluded air.

Table l BAKING RESULTS Percent Percent Percent otal Lactyl. Regular Emulsif Emulsit. Emulsif.

1 Code: A. Drumulse 9169. This boa mixture mitin, glyceryl dilacto mcuopalmitin, B. Lactylated mixed partial esters of G. Mono and diglycerides Mixed partial esters oi glycerol and propylene glycol with saturated fatty acids derived'irom 1 diglyceride. It appears to 1V. soybean oil.

stearine. D.

LV. soybean oil.

1 Both these cakes have Water..

EXAMPLE 1 For purposes of comparison, various emulsifiers were used in the following cake rrux batter:

Grams Flour 200 Sugar 232 Shortening 73 Baking powder 10 Salt 7 Non-fat milk solids 17 Whole eggs 100 236 Water very dark wet crusts and wet crumb which is not normal of a commercial lactylated fatty acid monoglyceryl dipalmit-in, glyceryl tripaland glyceryl monolacto dipalmitin.

material is an example or glyceryl moncpalmitln (alpha), glyceryl monolacto monopalnutin, glycerol and propylene glycol with saturated'iatty acids derived (tom l of saturated fatty. acids derived iroml LV. cottonseed winter. oil.

for this type cake.

characteristic.

EXAMPLE 2 Samples similar to (B) and (D) in Table I above were prepared with 1 LV. cottonseed winter oil stearine in place of the 1 LV. soybean oil, These samples gave essentially the same baking results as those shown for (B) and (D) above.

EXAMPLE 3 A fluid shortening was prepared by blending 5% of the lactylated mixed esters prepared above with 'I.V. soybean oil. The shortening had good fluidity and satisfactory baking character-tistics.

Higher levels of emulsifiers (A) While the invention has been described in terms of preferred embodiments thereof, it is to be understood that considerable variations in the detail disclosed may be made without departing from the true scope and spirit of the invention. Accordingly, the invention is to be limited only by the claims :set forth hereinafter.

I claim:

1. A cake mix comprising flour, baking powder and sugar intimately blended With a shortening comprising: (a) from about 8 to 16% by weight of the shortening of a mixture of lactylated higher fatty acid esters of glycerol and lactylated higher fatty acid esters of propylene glycol, from about to 90% by weight of said mixture being composed of lactylated propylene glycol higher fatty acid monoesters and (b) an edible triglyceride.

2. A cake mix comprising flour, baking powder and sugar intimately blended with a shortening comprising: (a) the reaction product of lactic acid and a mixture of the higher fatty acid esters of propylene glycol and the higher fatty acid esters of glycerol, from about 10 to 90% by weight of said reaction product being composed of propylene glycol higher fatty acid monoesters, (b) an emulsifier selected from the group consisting of edible nono-diglycerides and a mixture of the higher fatty acid esters of glycerol and the higher fatty acid esters of propylene glycol, and (c) an edible triglyceride the total amount of said reaction product (a) and emulsifier (b) in the shortening ranging from about 8 to 16% by weight thereof and the ratio of (a) to (b) being about 1:3 to 3: 1.

3. A porcess which comprises (a) heating a higher fatty acid triglyceride with an excess amount of a mixture of glycerol and propylene glycol in the presence of an esten'fication catalyst until an interesterified mixture of glycerol esters and propylene glycol esters is produced, (b) removing excess polyhydric alcohol from the reaction mixture and (c) slowly adding lactic acid to said mixture of esters at elevated temperatures until at least some of the free OM groups in the esters are lactylated to provide a final mixture containing about 10 to 90% by weight of propylene glycol higher fatty acid monoesters.

4. A mixture comprising (a) the esterification product of lactic acid and higher fatty acid esters of glycerol and (b) the esterification product of lactic acid and higher fatty acid esters of propylene glycol, the hydroxyl groups of the lactic acid residues in the mixture being substantially unesterified and from about 10 to by weight of the mixture being composed of lactylated higher fatty acid monoesters of propylene glycol.

5. The esterification product of lactic acid and a mixture of higher fatty acid esters of propylene glycol and higher fatty acid esters of glycerol, the hydroxyl groups of the lactic acid residues in said product being substantially unesterified and from about 10 to 90% by weight of the product being composed of lactylated propylene glycol higher fatty acid monoesters.

6. A shontening agent comprising an edible triglyceride and from about 8 to 16% by weight of the mixture of claim 4.

7. An emulsifier composition comprising: (a) the reaction product of lactic acid and a mixture of a higher fatty acid ester of propylene glycol and a higher fatty acid ester of glycerol, from about 10 to 90% by weight of said reaction product being composed of lactylated propylene glycol higher fatty acid monoesters and (b) an emulsifier selected from the group consisting of edible mono-diglycerides and a mixture of a higher fatty acid ester of gylcerol and a higher fatty acid ester of propylene glycol, the ratio of component (a) to component (b) ranging from about 1:3 to 3:1.

8. A shortening comprising an edible trigylceride in combination with from about 8 to 16% by weight of the emulsifier composition recited in claim 7.

References Cited in the file of this patent UNITED STATES PATENTS 2,329,166 Tucker Sept. 7, 1943 2,509,414 Barsky May 30, 1950 2,864,705 Schluman Dec. 16, 1958 2,874,051 Bedenk et a1 Feb. 17, 1959 2,970,055 Gleason Jan. 31, 1961 2,978,329 Cochrane et =al. Apr. 4, 1961 3,097,098 Allen et a1. July 9, 1963 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No 3,158,487 November 24 1964 Edward J, Reid It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

Column 4, line 12, for "minutes:" read minuteso column 5, line 30 for "porcess" read process same column 5, line 38 for "OM" read OH Signed and sealed this 6th day of April 1965@ (SEAL) Attest:

ERNEST W. SWIDER EDWARD J. BRENNER Attesting Officer Commissioner of Patents 

1. A CAKE MIX COMPRISING FLOUR, BAKING POWDER AND SUGAR INTIMATELY BLENDED WITH A SHORTENING COMPRISING: (A) FROM ABOUT 8 TO 16% BY WEIGHT OF THE SHORTENING OF A MIXTURE OF LACTYLATED HIGHER FATTY ACID ESTERS OF GLYCEROL AND LACTYLATED HIGHER FATTY ACID ESTERS OF PROPYLENE GLYCOL, FROM ABOUT 10 TO 90% BY WEIGHT OF SAID MIXTURE BEING COMPOSED OF LACTYLATED PROPYLENE GLYCOL HIGHER FATTY ACID MONOESTERS AND (B) AN EDIBLE TRIGLYCERIDE. 